(Z)-Stilbene Explained

(Z)-Stilbene is a diarylethene, that is, a hydrocarbon consisting of a cis ethene double bond substituted with a phenyl group on both carbon atoms of the double bond. The name stilbene was derived from the Greek word Greek, Ancient (to 1453);: stilbos, which means shining.

Isomers

Stilbene exists as two possible isomers known as (E)-stilbene and (Z)-stilbene. (Z)-Stilbene is sterically hindered and less stable because the steric interactions force the aromatic rings 43° out-of-plane and prevent conjugation.^[1] (Z)-Stilbene has a melting point of 5-, while (E)-stilbene melts around, illustrating that the two compounds are quite different.

Uses

• Stilbene is used in manufacture of dyes and optical brighteners, and also as a phosphor and a scintillator.
• Stilbene is one of the gain mediums used in dye lasers.

Properties

• Stilbene will typically have the chemistry of a diarylethene, a conjugated alkene.
• Stilbene can undergo photoisomerization under the influence of UV light.
• Stilbene can undergo stilbene photocyclization, an intramolecular reaction.
• (Z)-Stilbene can undergo electrocyclic reactions.

Natural occurrence

Many stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.

Notes and References

1. Book: Eliel . Ernest L. . Ernest L. Eliel . Wilen . Samuel H. . Stereochemistry of Organic Compounds . 1994 . John Wiley and Sons . 0-471-01670-5 . 566–567.